Successive waves of school reform since 1985 have brought about massive transformations in the roles and responsibilities of principals in Chicago Public Schools. The time period has also been marked by high principal turnover. This report presents findings of a study conducted in the fall of 1994 by the Department of Research, Evaluation, and Planning of the Chicago Public Schools (CPS). Researchers examined demographic data on CPS principals from personnel records, analyzed results of a 1992 survey of Chicago principals, and constructed an administrative history of all schools since 1987-88. They also conducted interviews with 61 former principals who had left their jobs after July 1, 1993. Findings show that after the 1989 wave of reform, the principalship became more accessible to women and minorities. However, few former principals reported that their academic training had been a key factor in preparing them for the job. Principals also require better-trained staff with more diverse knowledge and skills. The CPS should provide and require improved leadership training, institute continuous public recognition for successful schools and individuals, and disseminate information on successful change strategies. Three tables, seven figures, and eight endnotes are included. (Contains 55 references.) (LMI)